95977-53-0Relevant articles and documents
Synthesis and reactivities of enantiomerically pure β hydroxyalkyl and β-aminoalkyl ferrocenyl sulfides
Bernardi, Luca,Bonini, Bianca F.,Comes-Franchini, Mauro,Fochi, Mariafrancesca,Mazzanti, Germana,Ricci, Alfredo,Varchi, Greta
, p. 2776 - 2784 (2002)
Enantiomerically pure β-hydroxyalkyl and β-aminoalkyl ferrocenyl sulfides have been synthesized in good yields from mercaptoferrocene and amino alcohol derivatives. Primary β-aminoalkyl sulfides allowed the synthesis of tetrahydro-1,4-thiazepines containing the ferrocene moiety with good diastereoselectivity and β-iminoalkyl sulfides. Some of these derivatives have successfully been employed as ligands for palladium-catalyzed allylic substitution, with asymmetric induction of up to 99% ee. ( Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002).
Theoretical and Experimental Optimization of a New Amino Phosphite Ligand Library for Asymmetric Palladium-Catalyzed Allylic Substitution
Magre, Marc,Biosca, Maria,Norrby, Per-Ola,Pàmies, Oscar,Diéguez, Montserrat
, p. 4091 - 4107 (2015/12/26)
A new library of modular amino phosphite ligands obtained in a few synthetic steps from enantiopure amino alcohols has been tested in asymmetric Pd-catalyzed allylic substitution. The modular ligand design is crucial to find highly selective catalysts for each substrate type using a wide range of C-, N-, and O-nucleophiles. A DFT study of the species responsible for the enantiocontrol was used to optimize the ligand structure. By selecting the ligand components, we were able to identify unprecedented catalytic systems that can create new chiral C-C, C-N, and C-O bonds in a variety of substrate types (hindered and unhindered) in high yields and enantioselectivities (ee values up to 99 %). Further studies on the Pd-π-allyl intermediates provided a deep understanding of the effect of ligand structure in the origin of enantioselectivity. Potential applications of the new Pd/amino phosphite catalysts were demonstrated by the practical synthesis of a range of chiral carbocycles by simple tandem reactions, with no loss of enantioselectivity.
Dynamic resolution of N-Boc-2-lithiopiperidine
Coldham, Iain,Raimbault, Sophie,Chovatia, Praful T.,Patel, Jignesh J.,Leonori, Daniele,Sheikh, Nadeem S.,Whittaker, David T. E.
supporting information; experimental part, p. 4174 - 4176 (2009/03/11)
Dynamic thermodynamic resolution of N-Boc-2-lithiopiperidine is possible using a chiral ligand; the two enantiomers of this organolithium can be resolved with selectivities of up to 85: 15 from a selection of 26 chiral diamino-alkoxide ligands screened. The Royal Society of Chemistry.
